Jesse Sumner Cowles was born around 1845 to Sarah and Montgomery Cowles in Albemarle County, Virginia. Cowles had been a slave in eastern Virginia before the Civil War. When the Union army marched up the Virginia Peninsula toward Richmond in the summer of 1862, Cowles escaped slavery and fled to Union lines, becoming part of a mass wartime exodus of fugitive slaves to the Federal army. His family continued to live in the Williamsburg area during and after the war.

Cowles enlisted as a private at the age of 18 on November 30, 1863, in Hartford, Connecticut, and mustered in on March 8, 1864, in New Haven. His service record describes him as 5 feet, 5 1/2 inches tall, with black hair, black eyes, and dark complexion. Cowles served in the 29th Connecticut Infantry Regiment. With the 29th Connecticut, Cowles served throughout the South during the war, including at the siege of Petersburg and Richmond in 1864 and 1865 as well as in Maryland and Texas. Cowles received a wound to his left forearm at the Battle of Kell House (Second Fair Oaks), Virginia, on October 27, 1864. He mustered out with the rest of his regiment on October 24, 1865, in Brownsville, Texas.
 
After the war, Cowles made his way north to Connecticut, where he graduated from Wesleyan University and was ordained as a minister in 1872, playing a leadership role in the AME Zion churches in postings across the North. He used his considerable talents as an organizer and orator to support charitable causes, to protest segregation and other forms of discrimination, and to keep the memory of the Union victory alive. In 1885, for example, Cowles helped lead an effort to raise money in New York’s Black churches in order to erect a monument to the Union general and former president Ulysses S. Grant, who had just passed away.

He began receiving a pension of $6 a month in 1874. By 1890, he began receiving $10 a month until his death. Cowles died of consumption in York, Pennsylvania, on July 17, 1897. An obituary remembered him as "an earnest and faithful worker and an eloquent and pleasing pulpit orator." He is buried in Lebanon Cemetery in York along with his wife Nancy (Nannie) Cowles, who had died on November 4 the previous year. He was survived by his two adopted daughters: Etha, born November 1884; and Clara, born December 1886.

Documents:

Jesse S. Cowles Raises Money for Grant Monument Association

Jesse S. Cowles Joins Grant Monument Committee

Description of Jesse Cowles's Work as a Minister

Funeral of Jesse S. Cowles

Jesse Cowles Searches for His Family